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We quickly packed our stuff and left the school. As we walked towards the side street he made awkward small talk. We didn’t really know each other well and he was clearly fishing for something. Finally he just came out with it. “I never see you with any of the other guys; does your boyfriend go to another school?” I blushed and ducked my head. “I don’t really have one,” I mumbled. “I find that hard to believe.” He grinned and looked at me. “Why not?” I rolled my eyes. “Among the throngs of men throwing themselves at my feet there is not one who is worthy of my attention.” “Ouch!” He mimed being shot in the heart. “I guess that puts me in my place.” “I doubt it,” I shot back. My heart was racing. I was actually flirting back. And I was managing to not sound like too much of an idiot in the process. “Look at the abuse I’m willing to accept merely to be in your presence; surely that entitles me to a little favor?” “What kind of favor did you have in mind?” If only he knew, for him. I could see that a bit more had filled her. Jess grunted as he went in and moaned as he slowly pulled back out. Leonard repeated the slow withdrawal and reentry several more times until he was able to get about three quarters of it into the distended pussy without much difficulty. At that point, he increased his tempo quite a bit until he was pumping in and out of Jess's cunt in a steady rhythm. Jess was moaning steadily as Leonard picked up the pace, when he suddenly grabbed her ass in his hands and thrust forward abruptly while shoving her pussy down on his cock.Jess nearly screamed. "Oh god, what are you doing? You're going to tear me apart!" Suddenly, I saw her toes curl and her eyes nearly roll up in their sockets as she gasped and struggled for breath. Leonard had fucked her to a powerful orgasm that exploded out of nowhere. Jess made a keening noise and thrust down hard and I realized Leonard had buried himself to the hilt in the depths of her pussy. Her orgasm seemed to go on.
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